Methyl 4-(benzyloxy)-3-chloro-5-(cyclohexyloxy)benzoate → HCID 67041687, compound

HRID 62733Notes

Reaction equation

HRID 62733 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][C:10]=1[Cl:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCOCC1>[CH2:1]([O:8][C:9]1[C:18]([O:19][CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=1[Cl:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 67041669Methyl 4-(benzyloxy)-3-chloro-5-(cyclohexyloxy)benzoate

Product 1

HCID 67041687HCID 67041687, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-(Benzyloxy)-3-chloro-5-(cyclohexyloxy)benzoic acid (4) (329 mg, 97%) was prepared from methyl 4-(benzyloxy)-3-chloro-5-(cyclohexyloxy)benzoate (3) (350 mg, 0.934 mmol) using a procedure essentially the same as in Step (ii) for AAA-001, except that 1,4-dioxane (5 mL) was used instead of THF: m/z 359 [M−H]− (ES−); 1H NMR (400 MHz, DMSO-d6) δ: 13.19 (1H, s), 7.51 (2H, m), 7.48 (2H, m), 7.42-7.33 (3H, m), 5.10 (2H, s), 4.51 (1H, m), 1.94 (2H, m), 1.72 (2H, m), 1.59-1.49 (3H, m), 1.46-1.27 (3H, m).

Sources & evidence

ORD record
ord-cb042e6879f743f9b98c6cff961ef8f1
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

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